CN102161649A - Polyphenol type derivatives extracted from mulberry leaves and preparation method and applications thereof - Google Patents
Polyphenol type derivatives extracted from mulberry leaves and preparation method and applications thereof Download PDFInfo
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Abstract
The invention provides polyphenol type derivatives extracted from mulberry leaves. The polyphenol type derivatives contain a racemic compound (2R)/(2S)-7-methoxy-8-hydroxyethyl-2'4'-dihydroxyflavane and an epimeride mixture (2R/2S)-7-methoxy-8-ethyl-2'4'-dihydroxyflavane-2''-O-beta-D-glucopyranoside. The preparation method comprises the following steps: adding mulberry leaves in ethanol aqueous solution to heat and extract, concentrating, separating with a silica gel column, eluting, concentrating and drying eluent, further separating through the preparative liquid chromatography, collecting solution, concentrating and drying the collected solution to obtain a sample, and performing structural identification. The two polyphenol type derivatives provided by the invention has higher tyrosinase inhibitory activity and can be used in the preparations of the medicaments used for preventing and curing human pigmentation diseases and melanoma caused by the synthetic abnormality of melanin and other medicaments which are required to inhibit tyrosinase activity.
Description
Technical field
The invention belongs to the field of Chinese medicines, more specifically to Polyphenols derivative that from the Chinese medicine mulberry leaf, extracts and preparation method thereof and pharmaceutical applications with tyrosinase inhibitory activity.
Background technology
Mulberry leaf have another name called " Herba adianti myriosori ", belong to Moraceae Morus plant mulberry (
Morus albaL.).Mulberry leaf are stated from Shennong's Herbal as the medicinal beginning, its bitter, cold in nature, have enrich blood, effect such as dispelling wind, heat radiation, the ventilation of beneficial liver, antihypertensive diuretic.Modern a large amount of pharmaceutical research has proved that mulberry leaf have hypoglycemic, hypotensive, reducing blood-fat, removing free radical, anti-ageing, anti-inflammatory, many pharmacological actions such as antibiotic, antiviral and anticancer.The mulberry leaf chemical ingredients has flavones, steroidal, tonka bean camphor, volatile oil, alkaloid, amino acid, organic acid, VITAMIN and polysaccharide etc.
Tyrosine oxidase is as melanochrome synthetic key enzyme, and its unusual overexpression can cause the pigmentation disease of human body and melanoma etc.Therefore, tyrosinase inhibitor can be used as melanin inhibitor and is applied to medicine and other fields.
The present invention relates to derivative and preparation thereof that from mulberry leaf extraction separation has remarkable tyrosinase inhibitory activity, can effectively prevent and treat human pigmentation's property disease that the melanochrome resulting anomaly causes, melanoma and other to need the active illness of restraint of tyrosinase.
Summary of the invention
The object of the present invention is to provide a kind of Polyphenols derivative that from mulberry leaf, extracts, mainly comprise: racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane [(2R)/(2S)-7-methoxyl-8-hydroethyl-2', 4'-dihydroxylflavane] and (compd A) and epimer [(2R)/(2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside [(2R)/(2S)-and 7-methoxyl-8-ethyl-2', 4'-dihydroxylflavane-2''-O-β-D-glucopyranoside] (compd B).Its structure is as follows:
Another object of the present invention provides the preparation method of described Polyphenols derivative, realizes by following steps:
(1) with mulberry leaf with 70% ethanolic soln refluxing extraction, extract is evaporated to medicinal extract;
(2) medicinal extract is suspended in the suitable quantity of water, uses petroleum ether degreasing, ethyl acetate extraction;
(3) ethyl acetate extraction part is concentrated into medicinal extract, separates with purification on normal-phase silica gel, eluent is that volume ratio is sherwood oil and the ethyl acetate of 100:0 ~ 90:10; Volume ratio is sherwood oil and the ethyl acetate of 82:18; Volume ratio is sherwood oil and the ethyl acetate of 78:22 ~ 65:35; Volume ratio is sherwood oil and ethyl acetate and the ethyl acetate of 60:40;
(4) collected volume continues to separate the sample that obtains than for getting sample behind the sherwood oil of 60:40 and eluent ethyl acetate liquid and the eluent ethyl acetate liquid concentrate drying with preparative liquid chromatography respectively; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and methyl alcohol, gradient elution.
Step (4) collected volume gets sample than being the sherwood oil of 60:40 and eluent ethyl acetate liquid behind the concentrate drying, continue to separate the sample that obtains with preparative liquid chromatography, and the separation condition of preparative chromatography: chromatographic column is preparative column Agilent Zorbax SB-C
18Post 250 * 21.2 mm, 7 μ m, moving phase is water A and methyl alcohol B, the gradient elution program is as follows: 0 min, 30%B; 20 min, 50%B; 27 min, 50%B; 28 min, 60%B; 35 min, 60%B; 36 min, 70%B; 50 min, 70%B; 60 min, 80%B; Flow velocity: 10ml/min detects wavelength: 210nm.Collect the chromatographic peak of 47.5 min, decompression and solvent recovery gets compd A.
Step (4) is collected eluent ethyl acetate liquid, gets sample behind the concentrate drying, continues to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column: Agilent Zorbax SB-C
18Post 250 * 21.2 mm, 7 μ m, moving phase is water A and methyl alcohol B, the gradient elution program is as follows: 0 min, 25%B; 32 min, 44%B; 47 min, 44%B; 48 min, 55%B; 71 min, 60%B; 75 min, 100%B.Flow velocity: 10ml/min detects wavelength: 210nm.Collect the chromatographic peak of 72.3min, decompression and solvent recovery gets compd B.
A further object of the present invention provides human pigmentation's property disease that described Polyphenols derivative causes at preparation prevention and treatment melanochrome resulting anomaly, melanoma and other needs application in the active illness medicine of restraint of tyrosinase.
Polyphenols derivative provided by the invention can be used as activeconstituents, adds the auxiliary material of accepting on the pharmaceutics, makes preparation according to the preparation method of the preparation of putting down in writing on the pharmaceutics.
Described preparation comprises injection liquid, drip liquid, powder injection, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, sucks agent, granule, pill, paste, sublimed preparation, sprays, pill, disintegrating agent, orally disintegrating tablet, micropill etc.
Usefulness of the present invention is: the polyphenolic compound with tyrosinase inhibitory activity that extracts in two kinds of mulberry leaf that provide has the activity stronger than Folium Mori extract, make preparation and be easy to the quality control of medicine, human pigmentation's property disease that can cause at preparation prevention and treatment melanochrome resulting anomaly, melanoma and other need to use in the active illness of restraint of tyrosinase.
Embodiment
Further describe flesh and blood of the present invention and beneficial effect below in conjunction with embodiment, this embodiment only is used to the present invention is described but not limitation of the present invention.
Embodiment one racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', the preparation of 4'-dihydroxyl flavane
10 kg mulberry leaf are measured 70% alcohol reflux 2 times with 9 times, and each 2h is evaporated to medicinal extract, gets medicinal extract and is suspended in the suitable quantity of water, uses the petroleum ether extraction degreasing, separates water layer and uses ethyl acetate extraction again 6 times.With the ethyl acetate extraction part decompression and solvent recovery, 160 g medicinal extract, medicinal extract and 100-200 order silica gel by weight for after the ratio of 1:1 mixes thoroughly, are added in the silicagel column and separate.Eluent is that volume ratio is sherwood oil and the ethyl acetate of 100:0 ~ 90:10; Volume ratio is sherwood oil and the ethyl acetate of 82:18; Volume ratio is sherwood oil and the ethyl acetate of 78:22 ~ 65:35; Volume ratio is sherwood oil and ethyl acetate and the ethyl acetate of 60:40, and collected volume gets sample than being the sherwood oil of 60:40 and eluent ethyl acetate liquid behind the concentrate drying, continue to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and methyl alcohol, gradient elution.
The preparative liquid chromatography separation condition:
Instrument: Tianjin, island LC-8A preparative liquid chromatograph is equipped with the DAD detector.
Chromatographic column: Agilent Zorbax SB-C
18Post (250 * 21.2 mm, 7 μ m).
Moving phase: A phase: water; B phase: methyl alcohol.Linear elution gradient: 0 min, 30%B; 20 min, 50%B; 27 min, 50%B; 28 min, 60%B; 35 min, 60%B; 36 min, 70%B; 50 min, 70%B; 60 min, 80%B.Flow velocity: 10ml/min detects wavelength: 210nm.Collect the chromatographic peak of 47.5min, decompression and solvent recovery gets (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane.
Racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', the NMR (Nuclear Magnetic Resonance) spectrum and the mass-spectrometric data of 4'-dihydroxyl flavane are as follows:
1H?NMR?(500MHz,?DMSO-d
6):?δ?7.04?(1H,?d,?H-6'),?6.88?(1H,?d,?H-5),?6.48?(1H,?d,?H-6),?6.32?(1H,?d,?H-3'),?6.23?(1H,?dd,?H-5'),?5.15?(1H,?dd,?H-2),?3.72?(3H,?s,?OCH
3-7),?3.39?(1H,?m,?H-2''),?2.72?(1H,?m,?H-1''),?2.68,?2.82?(2H,?2m,?H-4),?1.79,?2.05?(2H,?2m,?H-3)。
13C?NMR?(500MHz,?DMSO-d
6):?δ?72.3?(C-2),?28.1?(C-3),?24.4?(C-4),?114.3?(C-4a),?127.1?(C-5),?103.0?(C-6),?156.4?(C-7),?113.2?(C-8),?153.7?(C-8a),?118.8?(C-1'),?154.8?(C-2'),?102.3?(C-3'),?157.5?(C-4'),?106.2?(C-5'),?126.9?(C-6'),?26.9?(C-1''),?60.0?(C-2''),?55.6?(OCH
3-7)。
ESI-MS:?m/z?315.21?[M-H]
-。
In the CD spectrum, be Δ ε=-0.0125 in the Cotton at 275nm place effect.
Structure elucidation shows that this compound is: (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane.
Embodiment two epimer mixtures [(2R)/(2S)-and 7-methoxyl group-8 ethyls-2', the preparation of 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside
The extraction of mulberry leaf, extraction, silica gel sepn process are with embodiment one, and different is to collect eluent ethyl acetate liquid, get sample behind the concentrate drying, continue to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and methyl alcohol, gradient elution.
The preparative liquid chromatography condition:
Instrument: Tianjin, island LC-8A preparative liquid chromatograph is equipped with the DAD detector.
Chromatographic column: Agilent Zorbax SB-C18 post (250 * 21.2 mm, 7 μ m).
Moving phase: A phase: water; B phase: methyl alcohol.Linear elution gradient: 0 min, 25%B; 32 min, 44%B; 47 min, 44%B; 48 min, 55%B; 71 min, 60%B; 75 min, 100%B.Flow velocity: 10ml/min detects wavelength: 210nm.Collect the chromatographic peak of 72.3min, decompression and solvent recovery gets epimer mixture (2R)/(2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside.
(2R/2S)-and 7-methoxyl group-8 ethyls-2', the NMR (Nuclear Magnetic Resonance) spectrum and the mass-spectrometric data of 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside are as follows:
1H?NMR?(500MHz,?DMSO-d
6):?δ?7.06?(1H,?d,?H-6'),?6.91?(1H,?d,?H-5),?6.51?(1H,?d,?H-6),?6.33?(1H,?d,?H-3'),?6.24?(H,?dd,?H-5'),?5.15?(1H,?dd,?H-2),?4.12?(1H,?d,?H-1'''),?3.75?(3H,?s,?OCH
3-7),?3.63,?3.45?(2H,?2m,?H-6'''),?3.44?(2H,?m,?H-2''),?3.12?(2H,?m,?H-3'''),?3.06?(H,?m,?H-4'''),?3.04?(H,?m,?H-5'''),?2.93?(H,?m,?H-2'''),?2.84?(H,?m,?H-1''),?2.64,?2.83?(2H,?2m,?H-4),?2.08,?1.79?(2H,?2m,?H-3)。
13C?NMR?(500MHz,?DMSO-d
6):?δ?72.6?(C-2),?28.0/28.1?(C-3),?24.4?(C-4),?114.4?(C-4a),?127.4?(C-5),?103.1?(C-6),?156.4?(C-7),?112.3?(C-8),?153.7/153.8?(C-8a),?118.7/118.8?(C-1'),?154.9/155.0?(C-2'),?102.3?(C-3'),?157.6?(C-4'),?106.2?(C-5'),?126.7?(C-6'),?23.4?(C-1''),?67.3?(C-2''),?55.6?(OCH
3-7),?102.8/103.0?(C-1'''),?73.5?(C-2'''),?76.9?(C-3'''),?70.0?(C-4'''),?76.8?(C-5'''),?61.0?(C-6''')。
ESI-MS:?m/z?477.33?[M-H]
-。
In the CD spectrum, be Δ ε=-0.040 in the Cotton at 275nm place effect.
Structure elucidation shows that it is: epimer mixture (2R/2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside.
The evaluation of embodiment trityrosine enzyme inhibition activity
The mulberry leaf total extract is made into 6.25,12.5, the solution of 25,50,100 μ g/ml concentration; With racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane and epimer mixture (2R/2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside is not made into 3.125,6.25,12.5, the solution of 25,50 μ mol/L concentration; The positive drug kojic acid is made into 6.25,12.5, the solution of 25,50,100 μ mol/L concentration.Get 96 orifice plates, add 250U/ml tyrosine oxidase 20 μ l, each concentration testing sample solution 20 μ l, and hatch 10min under 25 ° of C behind 100 μ l phosphate buffered saline buffers (100 mmol/L, the pH 6.8) mixing.Add reaction substrate again
3 mmol/L L-tyrosine, 20 μ l are hatched 30min under 25 ° of C behind the mixing.Measure its absorbance at the 492nm place.Enzyme solution wherein, sample solution, reaction substrate solution be all with 100 mmol/L, the preparation of pH 6.8 phosphate buffered saline buffers.
Enzymic activity inhibiting rate=[A
Blank-(A
Sample-A
Background)]/A
Blank* 100%
A
Blank: contain substrate and enzyme, do not add the reacted absorption value of testing sample;
A
Sample: contain substrate and enzyme, add the reacted absorption value of testing sample;
A
Background: contain substrate and testing sample, not enzyme-added absorption value.
The IC of mulberry leaf total extract
50Value is 68.04 μ g/ml, racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane and epimer mixture (2R/2S)-7-methoxyl group-8 ethyls-2', the IC of 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside
50Value is respectively 0.61 μ mol/L (0.19 μ g/ml) and 0.92 μ mol/L (0.44 μ g/ml), the IC of positive drug kojic acid
50Value is 17.29 μ mol/L (2.46 μ g/ml).
The preparation of embodiment four dropping pill formulations
Get racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2' with tyrosinase inhibitory activity, 4'-dihydroxyl flavane or epimer mixture (2R/2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside 0.1g and 10.5g polyoxyethylene glycol-20000 mix, heating and melting, move in the dripping pill drip irrigation after changing material, in ℃ whiteruss of medicine liquid droplet to 6 ~ 8, oil removing makes 400 of dripping pills.
The preparation of embodiment five lyophilized injectable powders
Get racemoid (2R)/(2S)-7-methoxyl group-8-hydroxyethyl-2' with tyrosinase inhibitory activity, 4'-dihydroxyl flavane and epimer mixture (2R/2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside 0.1g, glucose 4.5g, Sulfothiorine 0.9g and distilled water 1000ml, after said components mixes, 400 of packing, lyophilize, promptly.
Claims (7)
1. Polyphenols derivative that from mulberry leaf, extracts, it is characterized in that, described derivative mainly comprises: compd A: (2R)/(2S)-and 7-methoxyl group-8-hydroxyethyl-2', 4'-dihydroxyl flavane and compd B: (2R/2S)-7-methoxyl group-8 ethyls-2', 4'-dihydroxyl flavane-2''-O-β-D-glucopyranoside.
2. the preparation method of a kind of Polyphenols derivative that extracts from mulberry leaf according to claim 1 is characterized in that, realizes by following steps: (1) with mulberry leaf 70% alcohol reflux, extract is evaporated to medicinal extract; (2) medicinal extract is suspended in the suitable quantity of water, uses petroleum ether degreasing, ethyl acetate extraction; (3) ethyl acetate extraction part is separated with purification on normal-phase silica gel, eluent is that volume ratio is sherwood oil and the ethyl acetate of 100:0 ~ 90:10, volume ratio is sherwood oil and the ethyl acetate of 82:18, volume ratio is sherwood oil and the ethyl acetate of 78:22 ~ 65:35, and volume ratio is sherwood oil and ethyl acetate and the ethyl acetate of 60:40; (4) collected volume gets derivative than being the sherwood oil of 60:40 and eluent ethyl acetate liquid and eluent ethyl acetate liquid behind the concentrate drying respectively, continues to separate obtaining derivative with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and methyl alcohol, gradient elution.
3. according to claim 2 a kind of from mulberry leaf, extract the preparation method, it is characterized in that, compd A obtains by following steps: step (4) collected volume is than being the sherwood oil of 60:40 and eluent ethyl acetate liquid, get sample behind the concentrate drying, continue to separate the sample that obtains with preparative liquid chromatography, the separation condition of preparative chromatography: chromatographic column is preparative column Agilent Zorbax SB-C
18Post 250 * 21.2 mm, 7 μ m, moving phase is water A and methyl alcohol B, the gradient elution program is as follows: 0 min, 30%B; 20 min, 50%B; 27 min, 50%B; 28 min, 60%B; 35 min, 60%B; 36 min, 70%B; 50 min, 70%B; 60 min, 80%B; Flow velocity: 10ml/min detects wavelength: 210nm, collects the chromatographic peak of 47.5 min, and decompression and solvent recovery gets compd A.
4. according to claim 2 a kind of from mulberry leaf, extract the preparation method, it is characterized in that, compd B obtains by following steps: step (4) is collected eluent ethyl acetate liquid, gets sample behind the concentrate drying, continues to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column: Agilent Zorbax SB-C
18Post 250 * 21.2 mm, 7 μ m, moving phase is water A and methyl alcohol B, the gradient elution program is as follows: 0 min, 25%B; 32 min, 44%B; 47 min, 44%B; 48 min, 55%B; 71 min, 60%B; 75 min, 100%B, flow velocity: 10ml/min detects wavelength: 210nm, collects the chromatographic peak of 72.3min, and decompression and solvent recovery gets compd B.
5. a kind of Polyphenols derivative that extracts from mulberry leaf according to claim 1 is in human pigmentation's property disease that preparation prevents and treatment melanochrome resulting anomaly causes, the application in the melanoma medicine.
6. application according to claim 5 is characterized in that, described medicine adds acceptable auxiliary on the pharmaceutics by compd A or compd B, makes according to the formulation preparation method of putting down in writing on the pharmaceutics.
7. application according to claim 6 is characterized in that described preparation comprises liquid preparation or solid preparation.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105433388A (en) * | 2015-12-02 | 2016-03-30 | 西南民族大学 | Application of section moutan plant or extract of section moutan plant |
| CN109369582A (en) * | 2018-11-01 | 2019-02-22 | 中国科学院华南植物园 | A kind of dihydrofuran chalcone compounds and preparation method thereof |
| CN109438213A (en) * | 2018-10-29 | 2019-03-08 | 中国科学院华南植物园 | A kind of isopentene group chalcone compounds and preparation method thereof |
| CN109942428A (en) * | 2019-03-01 | 2019-06-28 | 重庆工商大学 | A kind of method that complex enzyme catalytic activation mulberry leaf obtain through refining high-purity chlorogenic acid |
| CN110615821A (en) * | 2019-09-17 | 2019-12-27 | 西北大学 | Mulberry extract, extraction and separation method and application thereof |
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| US20030125377A1 (en) * | 2001-08-07 | 2003-07-03 | Kinghorn Alan Douglas | Aromatase inhibitors from Broussonetia papyrifera |
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| US20030125377A1 (en) * | 2001-08-07 | 2003-07-03 | Kinghorn Alan Douglas | Aromatase inhibitors from Broussonetia papyrifera |
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| Title |
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| 《Journal of Natural Products》 20060318 Ah-Reum Han,et al Prenylated Flavonoids from the Heartwood of Artocarpus communis with Inhibitory Activity on Lipopolysaccharide-Induced Nitric Oxide Production 719-721 1-7 第69卷, 第4期 * |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105433388A (en) * | 2015-12-02 | 2016-03-30 | 西南民族大学 | Application of section moutan plant or extract of section moutan plant |
| CN109438213A (en) * | 2018-10-29 | 2019-03-08 | 中国科学院华南植物园 | A kind of isopentene group chalcone compounds and preparation method thereof |
| CN109438213B (en) * | 2018-10-29 | 2021-12-14 | 中国科学院华南植物园 | Isopentenyl chalcone compound and preparation method thereof |
| CN109369582A (en) * | 2018-11-01 | 2019-02-22 | 中国科学院华南植物园 | A kind of dihydrofuran chalcone compounds and preparation method thereof |
| CN109369582B (en) * | 2018-11-01 | 2021-12-10 | 中国科学院华南植物园 | Dihydrofuran chalcone compound and preparation method thereof |
| CN109942428A (en) * | 2019-03-01 | 2019-06-28 | 重庆工商大学 | A kind of method that complex enzyme catalytic activation mulberry leaf obtain through refining high-purity chlorogenic acid |
| CN110615821A (en) * | 2019-09-17 | 2019-12-27 | 西北大学 | Mulberry extract, extraction and separation method and application thereof |
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| CN102161649B (en) | 2012-07-04 |
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